以Pd(OAc)2为主催化剂,以Cu为助催化剂,以碘为氧化剂,高效地实现了吲哚与苯炔直接羰化合成吲哚-3-炔酮,并优化了反应条件.结果表明,该催化剂体系对带有不同取代基的吲哚、端炔类化合物具有非常好的适用性,最高分离产率可达94％.生成的吲哚-3-炔酮产物可进一步与叠氮化钠和溴苄一锅反应,高产率地得到3-甲酰三唑基吲哚类化合物.由于原料来源简单,产率高,且两类产物都是重要的中间体,因此该方法具有一定的应用价值.
参考文献
| [1] | Karpov A S;Merkul E;Rominger F;Müller T J J .[J].Angewandte Chemie International Edition,2005,44:6951. |
| [2] | Karpov A S;Müller T J J .[J].Organic Letters,2003,5:3451. |
| [3] | Wu X F;Neumann H;Beller M .[J].Chemical Society Reviews,2011,40:4986. |
| [4] | Liu, JM;Zhang, RZ;Wang, SF;Sun, W;Xia, C .A General and Efficient Copper Catalyst for the Double Carbonylation Reaction[J].Organic letters,2009(6):1321-1324. |
| [5] | Wu, X.-F.;Neumann, H.;Beller, M. .A general and convenient palladium-catalyzed carbonylative sonogashira coupling of aryl bromides[J].Chemistry: A European journal,2010(40):12104-12107. |
| [6] | Wu, X.-F.;Sundararaju, B.;Neumann, H.;Dixneuf, P.H.;Beller, M. .A general palladium-catalyzed carbonylative sonogashira coupling of aryl triflates[J].Chemistry: A European journal,2011(1):106-110. |
| [7] | Wu X F;Neumann H;Beller M .[J].Angewandte Chemie International Edition,2011,50:11142. |
| [8] | Giri R;Yu JQ .Synthesis of 1,2-and 1,3-Dicarboxylic Acids via Pd(II)-Catalyzed Carboxylation of Aryl and Vinyl C-H Bonds[J].Journal of the American Chemical Society,2008(43):14082-14083. |
| [9] | Guan, ZH;Ren, ZH;Spinella, SM;Yu, SC;Liang, YM;Zhang, XM .Rhodium-Catalyzed Direct Oxidative Carbonylation of Aromatic C-H Bond with CO and Alcohols[J].Journal of the American Chemical Society,2009(2):729-733. |
| [10] | Haffemayer B;Gulias M;Gaunt M J .[J].Chemical Sciences,2011,2:312. |
| [11] | Li FW;Xia CG .Synthesis of 2-oxazolidinone catalyzed by palladium on charcoal: a novel and highly effective heterogeneous catalytic system for oxidative cyclocarbonylation of beta-aminoalcohols and 2-aminophenol[J].Journal of Catalysis,2004(2):542-546. |
| [12] | 李福伟;彭新高;夏春谷;胡斌 .[J].中国化学,2005,23:643. |
| [13] | Peng XG;Li FW;Xia CG .A highly efficient sulfur-catalyzed oxidative carbonylation of primary amines and beta-amino alcohols[J].Synlett,2006(8):1161-1164. |
| [14] | Li F W;Xia C G .[J].Tetrahedron Letters,2007,48:4845. |
| [15] | Liu J M;Peng X G;Liu J H;Zheng S Z Sun W Xia C G .[J].Tetrahedron Letters,2007,48:929. |
| [16] | Zheng S Z;Xia C G .[J].Tetrahedron Letters,2007,48:5883. |
| [17] | Zheng SZ;Peng XG;Liu JM;Sun W;Xia CG .N-heterocyclic carbene-palladium complexes as efficient catalysts for the oxidative carbonylation of Amines to ureas[J].Helvetica chimica acta,2007(8):1471-1476. |
| [18] | 郑书展;彭新高;刘建明;孙伟 夏春谷 .[J].中国化学,2007,25:1065. |
| [19] | 彭新高,李福伟,胡霄雪,夏春谷,Christian A. SANDOVAL.Pd（Oac）2/[mmim]I催化体系胺氨化羰化合成氨基甲酸酯、脲和 2-（噁）唑啉酮[J].催化学报,2008(07):638-642. |
| [20] | 石利军,任业超,夏春谷,李福伟.双齿氮配体钯配合物催化的羰化反应研究[J].分子催化,2011(04):289-294. |
| [21] | Xue L Q;Shi L J;Han Y;Xia C G Huynh H V Li F W .[J].Dalton Transactions,2011,40:7632. |
| [22] | Lang, R.;Wu, J.;Shi, L.;Xia, C.;Li, F. .Regioselective Rh-catalyzed direct carbonylation of indoles to synthesize indole-3-carboxylates[J].Chemical communications,2011(46):12553-12555. |
| [23] | Lang, R.;Shi, L.;Li, D.;Xia, C.;Li, F. .A general method for palladium-catalyzed direct carbonylation of indole with alcohol and phenol[J].Organic letters,2012(16):4130-4133. |
| [24] | Xing, Q.;Shi, L.;Lang, R.;Xia, C.;Li, F. .Palladium-catalyzed mono- and double-carbonylation of indoles with amines controllably leading to amides and α-ketoamides[J].Chemical communications,2012(89):11023-11025. |
| [25] | Naruse Y;Ito Y;Inagaki S .[J].Journal of Organic Chemistry,1991,56:2256. |
| [26] | Gagosz F;Zard S Z .[J].Organic Letters,2002,4:4345. |
| [27] | Huang Y;Miao H;Zhang Q;Chen C Xu J .[J].Catalysis Letters,2008,122:344. |
| [28] | Li J;Zhang Y;Wang D;Wang W,Gao T,Wang L,Li J,Huang G,Chen B.[J].Synlett:Accounts and Rapid Communications In Synthetic Organic Chemistry,2010:1617. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%